


Be More Than My Weekend Boyfriend?

by DarkAngelGirl13



Category: Teen Wolf (TV)
Genre: Alternate Canon, Alternate Universe - Canon Divergence, Anal Fingering, Anal Sex, Bisexual Jackson Whittemore, Bisexual Male Character, Bottom Jackson Whittemore, Boyfriends, Boys Kissing, Canon Bisexual Character, Coming Out, Confessions, Dating, First Time, First Time Bottoming, Friendship/Love, Gay Male Character, Gay Sex, Good Theo Raeken, Hand Jobs, Kissing, Loss of Virginity, Love, Love Confessions, M/M, Mentioned Allison Argent, Mentioned Lydia Martin, Mentioned Scott McCall (Teen Wolf), Mentioned Stiles Stilinski, Not Canon Compliant, Oral Sex, Orgasm, Orgasm Delay/Denial, Secret Relationship, Sex, Top Theo Raeken
Language: English
Status: Completed
Published: 2019-12-11
Updated: 2019-12-11
Packaged: 2021-02-25 21:48:37
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,121
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21752518
Author URL: https://archiveofourown.org/users/DarkAngelGirl13/pseuds/DarkAngelGirl13
Summary: Theo has been Jackson's secret for four months only being together on the weekends. Jackson finally realizes that he can't keep doing just the weekends after something they share.
Relationships: Theo Raeken & Jackson Whittemore, Theo Raeken/Jackson Whittemore
Comments: 2
Kudos: 34





	Be More Than My Weekend Boyfriend?

**Author's Note:**

  * Inspired by [A Reason To Keep Living](https://archiveofourown.org/works/16087574) by [DarkAngelGirl13](https://archiveofourown.org/users/DarkAngelGirl13/pseuds/DarkAngelGirl13). 



> I Own Nothing
> 
> AN: Wrote this in either 2018 or early 2019 before computer problems. I just now found it again and the idea came in one of my other stories A Reason To Keep Living where had Theo with Stiles in that one.
> 
> AN2: This has been edited to fix the days from 12 to 32 since I really messed the adding up on that some how.

Jackson didn’t know why he couldn’t admit what he felt out loud. He couldn’t even bring his self to be nice unless he was alone with Theo. Right now they were just lying on his bed with Theo holding him. He had the TV on some channel he wasn’t even sure really since Theo had taken the remote from him. It was a lazy morning and they didn’t have to do anything since there wasn’t school on Saturday. It was one of the only two days he loved since it was the weekend. Saturday and Sunday was the two days out of all the rest that he spent alone with Theo. 

He’d turned his phone off Friday night when Theo had shown up after he’d gotten home and hadn’t turned it back on. Most weekends he didn’t until Sunday night when Theo left to go home. It was the day he hated, but it was his own fault since he was the one that couldn’t say the words out loud. He had tried more than once to tell Theo what he felt or just admit they were together. Theo put up with him wanting to stay a secret and he didn’t know why he did. The only thing he could think was that Theo was showing his love by not saying anything. 

Theo wasn’t paying attention to the TV that was playing some music video. He’d gotten tired of Jackson flipping stations so he’d put it on the music channel and tossed the remote. He didn’t want to waste time on watching anything. He knew it was borrowed time that he got to spend with Jackson. One day he was going to leave on Sunday night and Jackson wasn’t going to let him come back on a Friday night. He got every kiss and touch in that he could, he didn’t want to forget if this ended like he felt at times it would. He hadn’t really slept much the night before just watching how peaceful Jackson looked. 

He didn’t even care how much of an ass Jackson could be when they were at school. He had these moments knowing that these were the moments that Jackson was his self. The half of him that he kept from everyone else, probably even Danny, if he thought about it. He wasn’t even sure if Danny knew just how they were since for the last few months Danny hadn’t come around on the weekends. It was like some unspoken agreement that the weekends were just theirs. He kept his phone on vibrate in case Tara called. 

Otherwise he didn’t even bother looking at it unless he took a picture when Jackson didn’t notice. It was supposed to be the deal, no pictures, no communication outside of the weekend and being horrible to each other during the week. He just couldn’t follow the no pictures rule. He had them under a file on his phone with a password of Jackson’s name spelled backwards. 

Jackson rolled from his back onto his side pulling Theo’s face closer to him before he kissed him. They’d already had sex once that morning when he’d come back from the bathroom. He’d found Theo awake grinning at him like an idiot before he’d been yanked on the bed. Theo had pinned him down kissing him until they’d been out of breath. He’d flipped Theo over so he was under him. They’d made out until he’d grabbed the lube fucking Theo for the fourth time since he’d gotten to his house. 

Four months together, but only thirty two of them actually being together and he hadn’t let Theo fuck him yet. He wanted to, but he wasn’t ready to admit that he was bi. It was another one of the things that Theo put up with from him on top of the long list of others. He wasn’t stupid in knowing that Theo had broken the no pictures part of the deal. He’d been awake when Theo had taken the picture earlier. 

Jackson moved again so he was straddling Theo’s lap looking down into his eyes. He could feel his heart every time he was alone after Theo left him hurting. He didn’t want Theo to leave, but he couldn’t say the words. He shoved those thoughts back leaning down kissing Theo. He needed to get those thoughts from his mind now since they had another two days and a night until that happened. 

~JT TJ JT TJ~

Theo moved his hands over Jackson’s back kissing him back letting Jackson have control. He loved it when Jackson made the first move. It hadn’t been like that to start with even if it had only been about thirty-two days or nights they’d been together. Jackson had gotten better every week and it was almost perfect now. Theo moaned letting Jackson’s tongue into his mouth deepening the kiss. Jackson’s cock was leaking against his, which caused him to moan when Jackson moved against him. 

Jackson reached his hand between them taking hold of both their cocks in his hand moving it up and down. When he’d first started with Theo he hadn’t been able to leak at all before Theo had gotten him almost there. Now, he leaked like crazy and if Theo talked dirt to him he could cum untouched with just the right words. Theo pulled back gasping for air, moaning at how quick Jackson’s hand was moving. The friction of his hand and their cocks together was almost too much as it was. The pre-cum leaking out Jackson used to make their cocks even slicker. He was already close to cumming since while they’d been lying together Jackson had been lazily jerking him off for the last half an hour. He’d get close, but Jackson stopped before he’d cum. 

He did the same thing half the time to Jackson too, but he’d do other things besides just his hand. He’d used his mouth the weekend before on every place of Jackson’s body except his cock. He hadn’t let him get off until he was leaving that Sunday night either. Jackson had come close to breaking their rule of not talking that Monday too. He’d done the same by smiling at Jackson in the locker room shower when he’d walked by. Jackson had gone farther though since he’d actually reached out letting his hand graze him. Jackson was getting closer to cracking he knew, but until he did he couldn’t be the one that gave in.

Jackson let go of his cock before wrapping his hand almost all the way around Theo’s. Theo’s cock was thicker than his hand could cover if he tried wrapping it around it. He lacked about half an inch from wrapping it all the way around. Theo was a good inch longer than he was too, but he didn’t care. He had always wanted to be better at everything with Theo, but now that they were together the need had left him. He didn’t feel inadequate because Theo had showed him he didn’t need to feel that way when it came to their relationship. 

Jackson watched Theo as he moved his hand at a quicker pace. He didn't take his eyes off of him, until two weeks before that hadn't happened either. He wouldn't look at Theo while he'd been touching him. When Theo had been touching him he'd kept his eyes shut tight. He was learning though thanks to the one below him that he could let someone in, be loved. All the things he did and yet Theo put up with it for the time they spent together on weekends. 

~JT TJ JT TJ~

Jackson stopped before Theo got to the edge bending down crashing their mouths together. He swallowed the groan that Theo let out when he let go. He'd thought about it for the better part of the week as to what he wanted. When they broke apart from the kiss he reached for the lube that was under his pillow. He kept his eyes on Theo not able to say what he wanted, but it was like Theo could read his mind.

"I'll take care of you." Theo said taking the lube from Jackson getting him to lay down on his stomach. 

He set the lube beside them, but he moved Jackson's legs apart some before spreading his cheeks. He smiled before he flattened his tongue running it along Jackson's hole. He darted it in after a moment getting a shout from Jackson. He swirled, licked, drilled and nipped at Jackson's hole until he was a squirming mess below him. Jackson kept trying to hump the bed, but he held him down. He got him right on the edge before he stopped wanting them to cum together when he was inside.

He got the lube this time putting some on his fingers before he started working on opening Jackson up more. He worked his pinky finger in first since he didn't want to hurt his lover. Theo slowly progressed slipping each finger into Jackson before he started adding two at a time. Jackson moaned trying to stay still biting down on his hand just in case someone showed up at his bedroom door. He doubted it, but the week before his dad had almost caught them. 

As Theo worked two fingers into Jackson he started hitting his prostate too. He twisted, scissored, and curled his fingers loving the sounds Jackson was making. He bent down kissing Jackson's back and other spots. He even sucked at Jackson's cheeks not letting up until he saw the small bruise forming. By the time he got three fingers into Jackson he knew that if he didn't hurry Jackson wasn't going to last. He pulled his fingers free at the last second hearing Jackson let out a slew of cuss words as he denied him. 

~JT TJ JT TJ~

Theo got Jackson to turn back over so he was looking down at him. He'd slicked his cock up before he lined his self up. He got Jackson's legs up over his shoulder looking him dead into the eyes not daring to blink. He moved one of his hands over Jackson's stomach as he slid into him for the first time. He moaned feeling how tight Jackson was as if he was sliding into a glove made for him. 

Jackson moaned wanting to close his eyes as the feeling go too much, but he couldn't. It scared him, but he felt if he looked away he wouldn't forgive his self. Theo had said he'd take care of him and he was. He hadn't felt but a second of pain when he started filling him. The head had been what hurt the most, but it wasn't so bad when he got used to it. Theo had moved at snail speed until he was filling Jackson completely. He stayed still kissing Jackson until his cock was being clamped down on by Jackson. 

"Move please, just go slow." Jackson said hearing how he sounded. If it was anyone else right now he wouldn't even be in this position. He knew Theo wouldn't give him hell for sounding so fucking vulnerable right now. 

"As you wish, Jacks." Theo said giving Jackson a knowing smile before he bent down kissing him. 

Theo didn't let up on the kissing, if they needed air he moved to another part before going back to Jackson's lips. He kept the constant speed of a snails pace even when Jackson started moaning louder as he struck against his prostate. He brushed their noses together after one break from claiming Jackson's mouth. Another one he sucked at his nipples causing Jackson to let out a shout when he bit down just right. 

~JT TJ JT TJ~

He couldn't help but smile watching as Jackson's head kept turning from left to right when he was almost ready to cum. He was a puddle of goo below him and if he was a horrible person he might walk away or do something to expose this side of Jackson. He wasn't that person though, he'd been in love with Jackson since as long as he could remember. The start of those thirty-two days they'd had together wasn't their first kiss; that had been second grade. He had gone up to Jackson at Jackson's birthday party and kissed him. He'd said that was his gift to him since he couldn't think of anything better to give him. He'd ended up with a bloody nose sitting on his ass. It hadn't made him give up though and now he had what he'd wanted since the age of seven; Jackson as his. 

Jackson moaned feeling more pleasure than he thought was possible. He hadn't thought he'd like this at all, but he did. He didin't want Theo to stop, but he felt the knot in his stomach building even more. He could feel his balls rising until he was cumming with Theo's name tearing from him. He didn't care who might hear it was the best orgasm he'd had. Theo took hold of his cock finally touching him jerking him at the same pace he was now going. 

Theo felt his own orgasm a second after Jackson exploded between them. He pulled back thrusting in quicker than he had been doing. He kept switching it up with each new thrust inward nailing Jackson's prostate. He watched Jackson as he bucked up crying out again as he filled him. Theo didn't stop thrusting until the last rope landed inside of Jackson's tight passage. He fell forward barely catching his self, but Jackson flipped them over after his legs fell so he was lying on top of Theo still inside of him. 

Jackson laid there for a while feeling Theo's hands moving up and down his back; sides too. Theo gripped his ass squeezing and massaging it as they enjoyed the post orgasm haze. Theo didn't know how he was going to just ignore Jackson at school on Monday. He was just glad they still had more time of their secret world. He would do it though because he couldn't lose Jackson becasue he couldn't handle only having him Friday to Sunday nights.

"Once I recover you're doing that again, but actually fucking me mindless this time." Jackson said with a content sigh. He was going to enjoy the rest of the weekend. 

"Not a problem." Theo said wanting to give Jackson anything he asked for, for the rest of the weekend. 

~JT TJ JT TJ~

Jackson closed his locker Monday morning at school. He hadn't slept the night before when Theo had walked out of his bedroom. He'd been up all night thinking and came to the decision he couldn't do it anymore. He hadn't even gotten back around to fucking Theo, his ass had been filled the rest of the weekend. Theo hadn't just fucked him either. The rest of Saturday and all of that night Theo had found a reason to be in his ass. He'd just sat there watching a movie with Theo seated inside of him. He'd craved it, needing it, so he could feel connected; grounded. 

The only time he'd actually gotten dressed was when he'd walked Theo to the door. They had stood at the door for half an hour kissing. He had wanted to ask Theo to stay, but the deal had been he left Sunday night by eight. It gave them the time to go back to 'hating' each other. Some part of him had wanted Theo since he'd kissed him when they'd been kids. He just hadn't understood and he'd given Theo hell for the longest while. 

Jackson spotted Theo walking in the school with his usual friends Scott and Stiles; Allison was with them too. He met Theo's gaze across the hall and any will to hide what they had was broken. He forced his self to move from the lockers walking over to Theo who was surprised for sure. Unless he was going to go off on one of them he didn't go near them. He didn't give the other two hell only Theo since it was the one thing Theo had wanted if they couldn't be together in the open. 

He changed that though right then by pushing Theo back until his back hit the wall. He crashed their mouths together thrusting his tongue into Theo's mouth when he opened it in surprise. Jackson moaned feeling Theo's tongue as he sucked it until Theo started kissing him back. If they weren't in school he'd bend over somewhere and get Theo to fuck him. He felt empty since Theo had left him and he needed some kind of comfort. He didn't even care that he was telling the entire school he was with Theo. 

"Will you be my boyfriend, out in the open; not just on the weekends?" Jackson asked when he pulled back for air. 

Theo smiled wrapping his arms around Theo as tight as he dared loving the question he'd been asked. "Yes, I'll be out with you." He said feeling Jackson's arms around him just as tight. "I'll also fix what you are missing during free period." He grinned against Jackson's ear.

Jackson let a moan slip out at Theo's words knowing he knew his secret. He pulled back turning around, but instead of walking off without Theo he took hold of his hand. He closed his eyes for a moment before he walked away with Theo. Theo fell into step beside him only smiling at Scott and Stiles who were both shocked. Allison was giving him a smile and he knew that Lydia had probably told her something. Lydia was the reason that he'd even attempted to try and get Jackson. 

"Thank you, for saying yes. You could have said no and made me look stupid." Jackson said once they were in one of the classrooms.

"Why would I do that? You weren't the only one that's been enjoying the last four months. It was the best thirty-two days together, but now I can love you even more than those few days." Theo said bringing their mouths together showing Jackson what he felt for him. 

Jackson returned the kiss putting what he felt into it. He had come to another conclusion sitting in his room feeling alone the night before. "I.. I love you, too." He said in a low voice meeing Theo's eyes when he said it. 

"I know you do, Jacks. Never going to let you go either." Theo replied glad that he had taken his time getting to be with Jackson the way he had. 

~THE END~

**Author's Note:**

> Thanks in advanced for reviews and kudos


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